EP1178039B1 - Derivate von Phenyl(thio)harnstoff und Phenyl(thio)carbamat Fungiziden - Google Patents

Derivate von Phenyl(thio)harnstoff und Phenyl(thio)carbamat Fungiziden Download PDF

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EP1178039B1
EP1178039B1 EP01420173A EP01420173A EP1178039B1 EP 1178039 B1 EP1178039 B1 EP 1178039B1 EP 01420173 A EP01420173 A EP 01420173A EP 01420173 A EP01420173 A EP 01420173A EP 1178039 B1 EP1178039 B1 EP 1178039B1
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Prior art keywords
arch
radical
phenyl
alkyl
trifluoromethylphenyl
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EP01420173A
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English (en)
French (fr)
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EP1178039A1 (de
Inventor
Vincent Gerusz
Darren James Mansfield
José Perez
David Tickle
Jean-Pierre Vors
Derek Baldwin
Thomas Hough
Dale Robert Mitchell
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Bayer CropScience SA
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Bayer CropScience SA
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    • C07—ORGANIC CHEMISTRY
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    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/44—Iso-indoles; Hydrogenated iso-indoles
    • C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
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    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
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    • A01N47/38—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof
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    • C07C271/26—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring
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    • C07C275/34—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms having nitrogen atoms of urea groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
    • C07C275/36—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms having nitrogen atoms of urea groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring with at least one of the oxygen atoms further bound to a carbon atom of a six-membered aromatic ring, e.g. N-aryloxyphenylureas
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    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/20—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
    • C07D295/21—Radicals derived from sulfur analogues of carbonic acid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
    • C07D295/28—Nitrogen atoms
    • C07D295/32—Nitrogen atoms acylated with carboxylic or carbonic acids, or their nitrogen or sulfur analogues
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D307/18—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D307/20—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
    • C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
    • C07D317/58—Radicals substituted by nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/02—Systems containing only non-condensed rings with a three-membered ring

Definitions

  • the present invention relates to novel phenyl (thio) urea and phenyl (thio) carbamate fungicidal derivatives, process for their preparation and fungicidal compositions containing them.
  • the publication DE-3102590 discloses compounds whose general formula is as follows:
  • the essential technical characteristics for compounds disclosed by this document are the presence of an ester function and a 1,3-pyrazole group or a 1,2,4-trizaole in the presence of a nitrogen atom bound to a substituted phenyl.
  • the disclosed compounds for which biological activity is reported all have this ester function bonded in the ⁇ -position relative to the nitrogen atom bonded to the to the phenyl group.
  • the two examples of compounds 71 and 130 have not been synthesized, so they could not be tested biologically.
  • Complexes of the compounds according to the invention can be formed in the usual manner from a salt of formula NAn or NAn 2 , in which N represents a metal cation, for example copper, manganese, cobalt, nickel, iron or zinc and An represents an anion, for example chloride, nitrate or sulfate.
  • N represents a metal cation, for example copper, manganese, cobalt, nickel, iron or zinc
  • An represents an anion, for example chloride, nitrate or sulfate.
  • N-oxides of the compounds of the invention when these include an oxidizable nitrogen atom, are also within the scope of the present invention.
  • the invention includes individual isomers as well as mixtures thereof in all proportions.
  • the invention includes the individual isomers and tautomeric mixtures thereof in all proportions.
  • the invention comprises the individual isomers as well as mixtures thereof in all proportions, including the 50:50 mixture, said racemic mixture.
  • Any alkyl group defined above may be linear or branched and generally comprises from 1 to 10 carbon atoms, preferably from 1 to 7 carbon atoms, more preferably from 1 to 5 carbon atoms.
  • alkenyl or alkynyl groups defined above may be linear or branched, preferably comprise from 2 to 7 carbon atoms, and generally contain up to 3 double or triple bonds which may be conjugated, for example vinyl, allyl, butadienyl or propargyl.
  • the carbocyclyl groups may be saturated, unsaturated or aromatic and contain from 3 to 8 members.
  • Preferred saturated carbocyclyl groups include cyclopropyl, cyclopentyl, and cyclohexyl.
  • Preferred unsaturated carbocyclyl groups include up to 3 double bonds.
  • the term carbocyclic has the same definition in the present invention.
  • carbocyclyl includes any type of fused carbocyclyl moieties such as naphthyl, phenanthryl, indanyl and indenyl.
  • heterocyclyl groups may be saturated, unsaturated or aromatic and contain from 3 to 7 chaines, of which up to 4 of them may be heteroatoms such as nitrogen, oxygen and sulfur.
  • heterocyclyl group is meant for example furyl, thienyl, pyrrolyl, pyrrolinyl, pyrrolidinyl, imidazolyl, dioxolanyl, oxazolyl, thiazolyl, imidazolinyl, imidazolidinyl, pyrazolyl, pyrazolinyl, pyrazolidinyl, isoxazolyl, isothiazolyl, oxadiazolyl, triazolyl, thiadiazolyl, pyranyl, pyridyl, piperidinyl, dioxanyl, morpholino, dithianyl, thiomorpholino, pyridazinyl, pirimidinyl, pyrazinyl, piperazinyl
  • heterocyclyl includes fused heterocyclyl groups, for example benzimidazolyl, benzoxazolyl, imidazopyridinyl, benzoxazinyl, benzothiazinyl, oxazolopyridinyl, benzofuranyl, quinolinyl, quinazolinyl, qionoxalinyl, dihydroquinazolinyl, benzothiazolyl, phthalimido, benzofuranyl, benzodiazepinyl, indolyl and isoindolyl.
  • heterocyclic has the same definitions.
  • substituted qualifying the alkyl, alkenyl, alkynyl, carbocyclyl and heterocyclyl groups means that these groups may be substituted by one or more substituents, which may be identical or different, chosen from: hydroxy, alkenyl, alkynyl, mercapto, azido, nitro, halogen, cyano, acyl, alkoxycarbonyl, optionally substituted aminocarbonyl, optionally substituted amino, ammonia optionally substituted, optionally substituted carbocyclyl, optionally substituted heterocyclyl, cyanato, thiocyanato, -SF 5 ; -OR a ; -SR a ; -SOR a ; -SO 2 R a and -Si (R a) 3, with R a being alkyl, alkenyl, alkynyl, carbocyclyl or heterocyclyl, each of which may be optionally substituted.
  • substituents which may be identical or different,
  • the list further comprises alkyl, alkenyl and alkynyl, each of which may be optionally substituted.
  • Preferred substituents for the alkyl, alkenyl or alkynyl radicals are: alkoxy, haloalkoxy or alkylthio, each containing from 1 to 5 carbon atoms; halogen; or optionally substituted phenyl.
  • Preferred substituents for the carbocyclyl and heterocyclyl groups are: alkyl, haloalkyl, alkoxy, haloalkoxy or alkylthio, each containing from 1 to 5 carbon atoms; halogen; or optionally substituted phenyl.
  • alkyl radicals and carbon atoms of the carbocyclyl and heterocyclyl groups the list includes divalent radicals such as oxo or imino, optionally substituted by optionally substituted amino, R a or -OR a (where R a is as defined above).
  • Preferred radicals are oxo, imino, alkylimino, oximino, alkyloximino or hydrazono.
  • the amino groups when substituted and where appropriate, may be substituted with one or two identical or different substituents, chosen from: alkyl, alkenyl, optionally substituted alkynyl, optionally substituted amino, -OR a (where R a is such as previously defined), carbocyclyl, heterocyclyl and acyl.
  • substituents chosen from: alkyl, alkenyl, optionally substituted alkynyl, optionally substituted amino, -OR a (where R a is such as previously defined), carbocyclyl, heterocyclyl and acyl.
  • two substituents, with the nitrogen atom to which they are attached can form a heterocyclyl group, preferably a 5- to 7-membered heterocyclyl group, which may be substituted and which may contain other heteroatoms. for example morpholino, thiomorpholino or piperidinyl.
  • acyl includes the residues of sulfuric and phosphorus acids and also of carboxylic acids.
  • the present invention also provides a method for combating phytopathogenic fungi at a site that is infested or likely to be infested, which comprises applying therein a compound of formula (I) or a member thereof. salts.
  • the invention also provides a composition for agriculture comprising a compound of formula (I) or a salt thereof in admixture with an agriculturally acceptable diluent or carrier.
  • composition according to the invention may of course comprise more than one compound according to the invention.
  • composition may comprise one or more additional active ingredients, for example compounds known to possess plant growth regulator, herbicidal, fungicidal, insecticidal, acaricidal, antimicrobial or antibacterial properties.
  • additional active ingredients for example compounds known to possess plant growth regulator, herbicidal, fungicidal, insecticidal, acaricidal, antimicrobial or antibacterial properties.
  • the compound according to the invention can thus be used, for example, simultaneously, sequentially or alternatively with the other active material (s).
  • the diluent or support in the composition according to the invention may be a solid or a liquid in combination with a surfactant, for example a dispersing agent, an emulsifying agent or a wetting agent.
  • Suitable surfactants include anionic compounds such as a carboxylate, for example a metal carboxylate of a long chain fatty acid; N -acylsarcosinate; mono- or di-esters of phosphoric acid with ethoxylates of fatty alcohols or alkyl ethers of phenol or salts of such esters; sulphates of fatty alcohols such as sodium dodecyl sulphate, octadecyl sodium sulphate or sodium cetyl sulphate; sulfates of ethoxylated fatty alcohols; ethoxylated phenol alkyl sulfates; lignin sulfonates; petroleum sulfonates; alkyl-aryl sulf
  • Nonionic agents include condensation products of fatty acid esters, fatty alcohols, fatty acid amides or phenols substituted with alkyl- or alkenyl-fatty acids with ethylene oxide and / or propylene; fatty esters of ethers of polyhydric alcohols, for example sorbitan esters of fatty acids; condensation products of such esters with ethylene oxide, for example polyoxyethylene sorbitan fatty acid esters; alkyl glycoside products, alkyl polyglycoside products; block copolymers of ethylene oxide and propylene oxide; acetylenic glycols such as 2,4,7,9-tetramethyl-5-decyne-4,7-diol; ethoxylated acetylenic glycols; acrylic link graft copolymers; alkoxylated siloxane surfactants; or imidazoline surfactants, for example 1-hydroxyethyl-2-alkylimidazoline.
  • cationic surfactants include, for example, mono-, di- or polyamine, in the form of acetate, naphthenate or oleate; an amine containing oxygen, such as an amine oxide, a polyoxyethylene alkylamine or a polyoxypropylene alkylamine; an amide-bonded amine prepared by condensing a carboxylic acid with a di- or polyamine; or a quaternary ammonium salt.
  • compositions according to the invention may take any form in the field of the formulation of agrochemical compounds, for example, solution, aerosol, dispersion, aqueous emulsion, microemulsion, dispersible concentrate, powder for spraying, composition for coating or film-coating of seeds, composition for fumigation or fuming, dispersible powder, emulsifiable concentrate, granules or impregnated tape.
  • agrochemical compounds for example, solution, aerosol, dispersion, aqueous emulsion, microemulsion, dispersible concentrate, powder for spraying, composition for coating or film-coating of seeds, composition for fumigation or fuming, dispersible powder, emulsifiable concentrate, granules or impregnated tape.
  • agrochemical compounds for example, solution, aerosol, dispersion, aqueous emulsion, microemulsion, dispersible concentrate, powder for spraying, composition for coating or film-coating of seeds, composition for fumigation or
  • a dispersible concentrate comprises a compound according to the invention, dissolved in one or more solvents soluble in whole or in part in water, and one or more surfactants and / or polymers. Addition of the formulation to the water causes crystallization of the active material, the process being controlled by surfactants and / or polymers, resulting in fine dispersion.
  • a sprayable powder comprises a compound according to the invention mixed and thoroughly ground with a powdery solid diluent, for example, kaolin.
  • An emulsifiable concentrate comprises a compound according to the invention dissolved in a water immiscible solvent and which forms an emulsion or a microemulsion upon addition to water in the presence of an emulsifying agent.
  • a solid granule comprises a compound according to the invention combined with diluents similar to those which can be used for sprayable powders, the mixture being here granulated according to known methods.
  • the solid granule comprises the active material absorbed or coated on a preformed granulated support, for example Fuller's earth, attapulgite, silica or limestone grit.
  • Wettable powders, granules or granules usually comprise the active ingredient in admixture with suitable surfactants and an inert powder diluent such as clay or diatomaceous earth.
  • Another suitable concentrate is a flowable concentrate suspension formed by grinding the compound with water or other liquid, surfactants and a suspending agent.
  • the concentration of the active ingredient in the composition of the present invention, as applied to plants, is preferably from 0.0001 to 1.0 percent by weight, particularly from 0.0001 to 0.01 percent by weight. weight.
  • the amount of active ingredient may vary widely and may, for example, be from 5 to 95 percent by weight of the composition.
  • a compound of the invention When used, a compound of the invention is generally applied to seeds, plants or their habitat.
  • the compound can be applied directly to the soil before, at, or after seeding so that the presence of the active ingredient in the soil can control the growth of fungi that can attack the seeds.
  • the active ingredient In direct soil treatment, the active ingredient may be applied in any manner that allows it to be intimately mixed with the soil, such as by spraying, by solid granular diffusion or by application of the active ingredient at the same time as the seed using it in the same drill as the seeds.
  • a suitable application rate is between 5 and 1000 g per hectare, more preferably between 10 and 500 g per hectare.
  • the active ingredient can be applied directly to the plant, for example by spraying or dusting either when the fungus began to appear on the plant or before the appearance of the fungus as a protective measure.
  • the preferred mode of application is a spray on the leaves. It is usually important to get an effective fight against fungi at early stages of plant growth, since this is the time when the plant can be most severely damaged.
  • Spraying or dusting may conveniently contain a pre- or post-emergence herbicide, if necessary.
  • a suitable application rate is between 0.025 and 5 kg per hectare, preferably between 0.05 and 1 kg per hectare.
  • the compounds of the invention can be applied to fruits, vegetables or seeds harvested to prevent infection during storage.
  • the compounds according to the invention can be applied to the plants or parts thereof which have been genetically modified.
  • the compounds according to the invention can be used to treat fungal infections in timber and for application to public health.
  • the compounds of the invention may also be used to treat fungal infections in domestic or farm animals.
  • Compounds according to the invention can be prepared by many routes, according to known methods.
  • compounds of general formula (I) may be converted into other compounds of general formula (I) by derivatization of radicals R 0 or R 1 or R 2 or R 3 ; or by acylation, cyanation or alkylation when W represents O and R 0 or R 1 or R 2 or R 3 represent the hydrogen atom;
  • the compounds of general formula (III) can be prepared by reducing the nitro radical of the compounds of formula (IV) according to Scheme 3.
  • Preferred reaction conditions include a reaction with hydrazine hydrate in ethanol catalyzed by palladium or platinum;
  • the compounds of formula (IVa), that is to say the compounds of general formula (IV) in which A represents a radical A Z , can be prepared by reacting the compounds of formula (VI) with compounds of formula (VII) according to Scheme 7.
  • Z represents a radical which in compound (VI) forms an anion under basic conditions.
  • Z is alternatively a basic primary or secondary nitrogen atom.
  • X Z represents a leaving group, preferably a halogen atom.
  • preferred reaction conditions comprise treatment of (VI) with sodium hydride followed by addition of (VII).
  • reaction conditions include the reaction of (VI) with (VII) in the presence of a tertiary amine base such as ethyldiisopropylamine.
  • a tertiary amine base such as ethyldiisopropylamine.
  • preferred reaction conditions include the treatment of (VI) with potassium tert- butoxide in dimethylformamide at low temperature.
  • a Z represents a basic nitrogen atom, no base is required.
  • the compounds of formula (IVb), that is to say the compounds of general formula (IV) in which A represents a radical A W can be prepared by reaction of compounds of formula (VIII) with the compounds of formula ( IX) according to Scheme 8.
  • a W represents a radical which, in a compound (VIII), forms an anion under basic conditions.
  • X W represents a leaving group, preferably a halogen atom.
  • Preferred basic conditions include the reaction of (VIII) with carbonate carbonate carbonate or sodium hydride followed by the addition of (IX).
  • the compounds of formula (IVc), that is to say the compounds of general formula (IV) in which A represents O, can be prepared by reaction of compounds of formula (X) with boronic acids of formula (XI) according to Scheme 9.
  • Preferred reaction conditions include a reaction with copper acetate and triethylamine.
  • the compounds of formula (IVd), that is to say the compounds of formula (IV) in which A represents a direct bond can be prepared according to Scheme 10 from compounds of formula (XII) in which X Z represents a leaving group, preferably a halogen atom.
  • Compounds of formula (IV) in which A represents a direct bond and R 6 represents a heterocyclyl radical may be prepared using a variety of methods known to those skilled in the art (for example, see “Comprehensive Heterocyclic Chemistry", Vols 1-7 , AR Katritzky and CW Rees).
  • the routes of access to the compounds of formula (IV) containing a 1,2,4-oxadiazol-3-yl [compound (IVe)] and a 1,3,4-oxadiazol-2 radical -yl [compound (IVf)] are shown in Schemes 11 and 12.
  • the compounds of formula (IIIf), that is to say the compounds of general formula (III) in which A represents -CHR 7 - with R 7 representing a hydroxyl or alkoxy radical, may be prepared from compounds of formula (IIIg) according to the methodology described in Scheme 13, where R represents an optionally substituted alkyl radical or the hydrogen atom, and where R 6 represents an optionally substituted carboxy or hetero-cyclic radical which can form an anion in basic conditions.
  • reaction sequence described in Scheme 13 can be carried out on the compounds of formula (IIIf) in which the amine function is replaced by a precursor of the said function, for example the radical -NO 2 or the radical -N ( CW) R 0 .
  • the compounds of the general formula (I) can be prepared by introducing R 6 after the formation of the -NR O (CW) Y entity.
  • the compounds of the invention can be prepared using the well-known techniques of combinatorial chemistry.
  • the invention is illustrated by the following Examples but should not be construed as limited by them.
  • the structures of the novel, isolated compounds were confirmed by NMR and / or other appropriate assays.
  • the proton NMR spectra ( 1 H NMR) were recorded in deuterochloroform and the chemical shifts ( ⁇ ) are given in parts per million relative to tetramethylsilane.
  • Table 1 illustrate, in a nonlimiting manner, some compounds according to the present invention which have been synthesized from the preceding procedures.
  • CH2 means CH 2
  • CO2 means CO 2 , etc.
  • Aqueous solutions or dispersions of the compounds at the desired concentration, including one or more wetting agents, are applied by spraying or soaking the base of the test plant stem, as appropriate. After a given time, the plants or parts of the plants are inoculated with the appropriate test pathogens, and stored under controlled environmental conditions suitable for maintaining plant growth and disease development. After a suitable time, the degree of infection of the infected part of the plant is estimated visually. At a concentration of 500 ppm (w / v) or less, the following compounds have a control of at least 65% efficacy against the specified fungal diseases compared to an untreated control.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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  • Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
  • Other In-Based Heterocyclic Compounds (AREA)
  • Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
  • Pyrrole Compounds (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Furan Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Indole Compounds (AREA)

Claims (6)

  1. Verbindungen der allgemeinen Formel (I) sowie ihre Salze:
    Figure imgb0127
     worin
    • W für O oder S steht;
    • Y für einen Rest -NR1R2, -OR3 oder -SR3 steht;
    • R0 für einen Alkylrest oder ein Wasserstoffatom steht;
    • R1 und R2, die gleich oder verschieden sein können, für einen Alkyl- oder Acylrest, von denen jeder mit einem Alkoxy substituiert sein kann; oder ein Wasserstoffatom; oder NRaRb, ORa stehen, worin Ra und Rb, die gleich oder verschieden sein können, für einen Alkyl-, Acyl- oder Carbocyclylrest stehen, von denen jeder substituiert sein kann;
    • R3 für einen Alkyl- oder Acylrest, von denen jeder mit einem Alkoxy substituiert sein kann; oder ein Wasserstoffatom steht;
    • R1 und R2 oder R1 und R0 oder R3 und R0 oder Ra und Rb zusammen mit den Atomen, die sie verbinden, einen gegebenenfalls substituierten Ring bilden können, wobei die Gesamtheit so eine Carbocyclyl- oder Heterocyclylgruppe bildet;
    • R4 für einen Alkylrest steht, der mit einem Halogenatom substituiert sein kann;
    • R5 für einen Alkyl- oder Acylrest, von denen jeder substituiert sein kann; oder ein Wasserstoffatom steht;
    • R6 für einen Phenylrest oder einen aromatischen Heterocyclylrest steht;
    • A für -O- oder -S- steht.
  2. Verbindungen nach Anspruch 1, worin:
    • R° für einen Alkylrest oder ein Wasserstoffatom steht;
    • R1, R2 und R3 wie vorstehend definiert sind;
    • R4 für einen Alkylrest steht, der mit einem Halogenatom substituiert sein kann;
    • R5 für einen Alkylrest steht, der mit einem Halogenatom substituiert sein kann;
    • A für die zweiwertigen Reste -0- oder -S- steht; und
    • R6 für einen Phenylrest oder einen aromatischen Heterocyclylrest steht.
  3. Verbindungen nach einem der vorstehenden Ansprüche, die die folgenden Eigenschaften allein oder in Kombination besitzen:
    • R4 steht für einen C1-C10-Alkylrest;
    • R5 steht für einen C1-C10-Alkylrest;
    • A steht für den zweiwertigen Rest -O- und besetzt die Position 4 am Benzolkern M;
    • R6 steht für einen Phenylrest.
  4. Verwendung der Verbindungen nach einem der vorstehenden Ansprüche als Fungizide.
  5. Fungizide Zusammensetzung, die mindestens eine Verbindung nach einem der Ansprüche 1 bis 3 oder eines ihrer Salze im Gemisch mit einem landwirtschaftlich annehmbaren Verdünnungsmittel oder Träger umfasst.
  6. Verfahren zur Bekämpfung phytopathogener Pilze an einer Stelle, die davon befallen ist oder empfänglich dafür ist, davon befallen zu werden, umfassend das Aufbringen einer Verbindung nach einem der Ansprüche 1 bis 3 oder eines ihrer Salze auf diese Stelle.
EP01420173A 2000-08-04 2001-08-01 Derivate von Phenyl(thio)harnstoff und Phenyl(thio)carbamat Fungiziden Expired - Lifetime EP1178039B1 (de)

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US6696487B2 (en) 2004-02-24
DK1178039T3 (da) 2007-05-07
ATE359265T1 (de) 2007-05-15
PT1178039E (pt) 2007-06-26
EP1178039A1 (de) 2002-02-06
US20030008884A1 (en) 2003-01-09
DE60127772T2 (de) 2007-12-27
DE60127772D1 (de) 2007-05-24
JP2002114751A (ja) 2002-04-16
ES2284605T3 (es) 2007-11-16

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